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Sigma-Aldrich

(Triphenylphosphoranylidene)acetaldehyde

95%

Synonym(s):

(Formylmethylene)triphenylphosphorane

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About This Item

Linear Formula:
HCOCH=P(C6H5)3
CAS Number:
2136-75-6
Molecular Weight:
304.32
Beilstein:
523797
EC Number:
218-375-6
MDL number:
MFCD00006994
UNSPSC Code:
12352114
PubChem Substance ID:
24856960
NACRES:
NA.22

Assay

95%

form

solid

reaction suitability

reaction type: C-C Bond Formation

mp

185-188 °C (lit.)

SMILES string

[H]C(=O)C=P(c1ccccc1)(c2ccccc2)c3ccccc3

InChI

1S/C20H17OP/c21-16-17-22(18-10-4-1-5-11-18,19-12-6-2-7-13-19)20-14-8-3-9-15-20/h1-17H

InChI key

CQCAYWAIRTVXIY-UHFFFAOYSA-N

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Application

Wittig reagent for the conversion of aldehydes and ketones to two-carbon homologated, α,β-unsaturated carbonyl compounds.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315,H319,H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Jian Wang et al.
Organic letters, 9(18), 3703-3706 (2007-08-19)
The first total synthesis of (-)-aplysiallene has been completed in 16 steps and features a key sequential Mukaiyama aerobic oxidative cyclization to prepare the fused bis-THF core. The original stereochemical assignment has been revised as shown.
Tohru Nagamitsu et al.
The Journal of organic chemistry, 72(8), 2744-2756 (2007-03-16)
The total synthesis of borrelidin has been achieved. The best feature of our synthetic route is macrocyclization at C11-C12 for the construction of an 18-membered ring after esterification between two segments. A detailed examination of the macrocyclization led us to

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